5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → 2-[2-(2-Dimethylaminomethyl-5-furylmethylthio)ethylamino]-5-[1-(2-dimethylaminoethyl)-2-oxopyridin-4-ylmethyl]pyrimidin-4-one

HRID 1719553Notes

Reaction equation

HRID 1719553 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:6][C:7]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[CH:8][CH:9]=1)[CH3:3].[N+](N[C:19]1[NH:24][C:23](=[O:25])[C:22]([CH2:26][C:27]2[CH:32]=[CH:31][N:30]([CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[C:29](=[O:38])[CH:28]=2)=[CH:21][N:20]=1)([O-])=O>N1C=CC=CC=1>[CH3:3][N:2]([CH2:4][C:5]1[O:6][C:7]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:19]2[NH:24][C:23](=[O:25])[C:22]([CH2:26][C:27]3[CH:32]=[CH:31][N:30]([CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[C:29](=[O:38])[CH:28]=3)=[CH:21][N:20]=2)=[CH:8][CH:9]=1)[CH3:1]

Participants

4

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 703541452-Nitroamino-5-[1-(2-dimethylaminoethyl)-2-oxopyridin-4-ylmethyl]pyrimidin-4-one

Product 1

HCID 703539102-[2-(2-Dimethylaminomethyl-5-furylmethylthio)ethylamino]-5-[1-(2-dimethylaminoethyl)-2-oxopyridin-4-ylmethyl]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(2-Dimethylaminomethyl-5-furylmethylthio)ethylamine (4.00 g) and 2-nitroamino-5-[1-(2-dimethylaminoethyl)-2-oxopyridin-4-yl-methyl]pyrimidin-4-one (7.14 g) were refluxed in pyridine (50 ml) for 24 hours. The reaction mixture was evaporated under reduced pressure and the residue subjected to medium pressure column chromatography (Kieselgel 60 silica mesh - main column) using ethyl acetate:methanol (80:20→70:30) gradient elution. The fractions containing the desired title product were evaporated in vacuo and treated with maleic acid (1.79 g) in isopropanol. The solvent was evaporated under reduced pressure and the residue washed with acetone and cold isopropanol. On standing at 5° C. the residue crystallised from ethanol-methanol to yield 2-[2-(2-dimethylaminomethyl-5-furylmethylthio)ethylamino]-5-[1-(2-dimethylaminoethyl)-2-oxopyridin-4-ylmethyl]pyrimidin-4-one as a maleate salt (0.79 g), m.p. 123°-126° C.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. washethyl acetate:methanol (80:20→70:30) gradient elution
  3. additionThe fractions containing the desired title product
  4. customwere evaporated in vacuo
  5. additiontreated with maleic acid (1.79 g) in isopropanol
  6. customThe solvent was evaporated under reduced pressure
  7. washthe residue washed with acetone and cold isopropanol
  8. customOn standing at 5° C.
  9. customcrystallised from ethanol-methanol

Sources & evidence

ORD record
ord-763d0089c6a74b9f975f36ef3addb3d7
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

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